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The Hamilton Family

Above: (l-r) William Hamilton, Lucy Young Hamilton, Fernanda Kimball,Austin Kimball, Alexandra Kimball, William “Billy” Kimball


Drawing a Crowd: 

A Family Remembrance of William Hamilton, 1930 - 2016

Billy Kimball

Although people sometimes did, there was no real reason to ask William Hamilton where he got his ideas for his cartoons. Set in the haute bourgeois world of ballrooms, boudoirs, and boardrooms and peopled with characters who might be described as “privileged,” it was a crowd and a milieu that William knew well (though his actual time spent in boardrooms was limited.) While his readers may not themselves have had firsthand experience with the somewhat rarified environments, his cartoons sought to present subtle and universal truths about human nature that transcended barriers of class and time. In his hands, their somewhat exclusive, somewhat retrograde settings—an opera box, the owners’ circle at the track, gentlemen’s clubs and the like—became inclusive.


In particular, the dilemmas his cartoons addressed, about insecurity, about the baffling complexities of social ritual, about the ineluctable power of basic human drives in people of all classes, and about the wistful nostalgia that comes with the passage of time, are broadly felt. In William’s hands, a debutante’s fleeting moment of doubt, a CEO’s temporary flare of honesty, or a bored trophy wife’s revealing confidences about her husband, become moments from all of our lives, no matter where or who we are.


William knew human beings as social creatures. His cartoons are invariably about conversation: groups of people— sometimes couples, sometimes slightly larger groups, though never a multitude—interacting. We may see only one side of the discussion but we know that there’s always a discussion. His work was about the moments that define our private lives, which, in turn, form such a large, though somewhat hidden, part of our culture. His insights struck home with his readers because they felt a sense of recognition in his cartoons, not because, God forbid, they saw themselves necessarily, but because they thought they saw people they knew. In this way, he allowed his readers to let themselves off the hook personally, though, perhaps, he gave them food for thought.

Above: Gilliam Hamilton


Billy Kimball is a writer and producer, mostly for television. He has written for The Simpsons and Saturday Night Live and is currently a writer and supervising producer for HBO’s Veep. For that work, he shared the 2016 Emmy for “Best Comedy.” Born in New York City, he graduated from Harvard College where he was an editor of The Harvard Lampoon. He lives with his wife, the former Alexandra Hamilton, on Key Biscayne in South Florida with their two children, Fernanda and Austin. An older daughter, Sophie, is a senior at Harvard.


William Hamilton was his father-in-law.

If William’s reality was a little different than most people’s, at least it was, he would say, real. He never drew a man standing on a street corner holding up a sign announcing the end of the world, two dogs talking, or a king speaking to a condemned prisoner. He aimed for a certain kind of satire grounded in reality that he felt his readers would respond to more deeply because they would recognize its well-observed validity, as opposed to a cartoon that simply told a joke.


Although a native son of the Golden West, there was a particularly New York quality to William’s work that made it especially appealing to readers of The New Yorker. In a city that seethes with aspiration and where people are preoccupied with subtle social rituals, his work suggested that the world of Manhattan sophistication so many aspire to might be beset with the same sort of frustrations, insecurities, and tedium as the life of anyone anywhere.


Raised in idyllic and genteel, if somewhat nouveau pauvre, circumstances at Ethelwild, the ranch in the Napa Valley that had belonged to his family since the Civil War, William was, in due course, sent off to Andover and eventually Yale. William’s eccentric father was devoted to Quixotic pursuits like converting the world to a “metric clock” that would have a 10-hour day and the belief that money would become obsolete in his lifetime (it didn’t). After a stint in the Army, where the closest he came to combat was a fist-fight sparked by a sarcastic review he wrote of the film playing at his base in the Aleutians, William commenced his pursuit of his chosen profession: cartoonist.


When William sold his first cartoon to The New Yorker in 1965, cartooning was at the end of a long heyday. Besides The New Yorker, Playboy, The Saturday Evening Post, and many other magazines all ran cartoons. One could make a living at it, he insisted, though the story of his first meeting with The New Yorker’s legendary William Shawn suggests that maybe it wasn’t an exceptionally rich living. According to William, Shawn’s opening gambit was, “So, Mr. Hamilton, you would like to be a cartoonist. Tell me, have you any money?” When William responded that he really didn’t, Shawn turned away and said, wistfully, “Ah. Pity.”


The New Yorker remained homebase for William for the rest of his life, during which it published more than 2,000 of his cartoons. In his spare time, he wrote three novels and a number of plays, the best known of which is Saving Grand Central. But he was a cartoonist, first and very much foremost.  He worked every day, generally drawing the picture first, sometimes without a specific idea of the caption, and then would come up with multiple possible captions for a drawing—say, of two men talking at a bar or a husband and wife dressing for a party.


Those who knew and appreciated his sense of humor usually have a favorite William Hamilton cartoon. (According to no less an authority than The Preppy Handbook, one of the indicators that one is in a genuinely preppy household is a William Hamilton cartoon on the refrigerator.) The ones I think of most often reflect some acute insight about our anxious age, like one where a wife suggests to her husband, “Maybe you’re not underrated,” or when a husband dressed in black tie asks his wife, “If we don’t go, do you think people will think we weren’t invited?” Wall Streeters and their ilk were another frequent target. At a boardroom huddle, one irritated director says to another, “Everyone sees through your damned transparency!”


William’s later work is also suffused with somewhat surprised nostalgia, a sense of fin de siècle, that the world had changed in certain slightly undesirable ways, seemingly overnight.  “Another thing I love about drinking is that you can’t do it on-line,” says a man sharing a bottle with a friend. Another one shows a typical mob in an airport wearing shorts, shower shoes and t-shirts with vulgar sayings printed on them. A man dressed much like William always did to travel, in a sports coat, corduroys, and loafers, wonders “Whatever happened to the jet set?” (It may be worth mentioning that William, who at 6'5" was physically imposing, was always impeccably tailored and shod. Had you encountered him on the street and tried to guess his occupation, “cartoonist” would probably have come in last.)


Breaking the taboo of speaking frankly about money appealed greatly to William’s sense of mischief. A regular weekly cartoon, “Money Can Be Fun,” generally tweaking plutocrats and our plutocracy, ran for a time in the New York Observer. “New money is just old money that got away,” is one highly quotable caption. A friend, the writer Michael Tolkin, has a favorite William Hamilton cartoon showing a couple looking at another couple from afar at a cocktail party. The bone-dry caption is, “They have a lot of, you know…money.”


Now, the fact is that I’ve looked for this cartoon and have never actually been able to find it, suggesting that perhaps William’s style and voice were so distinctive that people sometimes created their own Hamiltons in their minds and then gave him credit. Proof, I think, of his broad and quite specific influence.


Now that William himself is gone, his body of work, accessible through The New Yorker’s Cartoon Bank still offers us his wit, his insight, and his portrait of a world that, though a bit faded on the surface, will always exist as long as some people have more than they need, some want more than they have, and people pursue pleasure as distraction, lament the past, fear the future, eat, drink, and fall in love. In other words, forever.


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